Skip to Content
Merck
All Photos(1)

Documents

A129

Sigma-Aldrich

Amoxapine

Synonym(s):

2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C17H16ClN3O
CAS Number:
14028-44-5
Molecular Weight:
313.78
EC Number:
237-867-1
MDL number:
MFCD00069210
UNSPSC Code:
12352200
PubChem Substance ID:
24278075
NACRES:
NA.77

form

powder

solubility

methanol: soluble

originator

Wyeth

SMILES string

Clc1ccc2Oc3ccccc3N=C(N4CCNCC4)c2c1

InChI

1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

InChI key

QWGDMFLQWFTERH-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , SLC6A2(6530) , SLC6A4(6532)

Looking for similar products? Visit Product Comparison Guide

Application

Amoxapine has been used as an antidepressant drug to test its effect on locomotion and egg release in response to gain-of-functional mutations in potassium (K+) channels (unc-58) of C. elegans. It has also been used as an antipsychotic drug to test its effect on the viability of glioblastoma cells.

Biochem/physiol Actions

Amoxapine, a structural analog of clozapine, is a human ether a-go-go (hERG) channel blocker. It is also an N-methylated metabolite of loxapine. It is a tricyclic antidepressant that inhibits the uptake of norepinephrine and blocks 5- hydroxytryptamine (HT2 ) serotonergic receptors.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

S G Jue et al.
Drugs, 24(1), 1-23 (1982-07-01)
Amoxapine is an N-demethylated dibenzoxazepine closely related in the neuroleptic loxapine. Its tricyclic structure appears to give it antidepressant properties resembling imipramine and amitriptyline. In uncontrolled trials it was shown to have antidepressant activity in usual doses up to 200
S Kapur et al.
Biological psychiatry, 45(9), 1217-1220 (1999-05-20)
All currently available atypical antipsychotics have, at clinically relevant doses: i) high serotonin (5-HT)2 occupancy; ii) greater 5-HT2 than dopamine (D)2 occupancy; and iii) a higher incidence of extrapyramidal side effects when their D2 occupancy exceeds 80%. A review of
Imran B Chaudhry et al.
Journal of clinical psychopharmacology, 27(6), 575-581 (2007-11-16)
It has been proposed that the lack of extrapyramidal side effects of atypical antipsychotic drugs is caused by their fast dissociation or low affinity for the D2 receptor or their concomitant high affinity for other receptors, for example, 5HT2 and
Yan-Lin He et al.
The Journal of pharmacology and experimental therapeutics, 332(2), 437-445 (2009-11-17)
Ion channels are known to be modulated by antidepressant drugs, but the molecular mechanisms are not known. We have shown that the antidepressant drug amoxapine suppresses rectifier outward K(+) (I(K)) currents in mouse cortical neurons. At a concentration of 10
F Jenck et al.
Progress in neuro-psychopharmacology & biological psychiatry, 18(3), 563-574 (1994-05-01)
A variety of antidepressants of different chemical classes were tested for their in vivo and in vitro activity at 5-HT1C receptors in the brain. Conventional tricyclic antidepressants (imipramine, desipramine, maprotiline, clomipramine, trimipramine, amitriptyline, nortriptyline, doxepin, amoxapine, oxaprotiline) and two atypical
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service